To overcome customer inertia with AI, don't pitch a broad platform. Instead, identify a specific, high-impact use case for their industry (e.g., 'where's my order' for retail). Deliver a pilot that shows tangible, quick value, and use that success as a beachhead to expand to other use cases.

To convince executives at traditional companies of AI's potential, abstract presentations fail. Instead, provide tangible, immersive experiences. A ride in a Waymo car, for instance, serves as a powerful product demo that makes the future feel concrete and inevitable, opening minds in a way slideshows cannot.

Generic use cases fail to persuade leadership. To get genuine AI investment, build a custom tool that solves a specific, tangible pain point for an executive. An example is an 'AI board member' trained on past feedback to critique board decks before a meeting, making the value undeniable.

The viral experimentation with the AI tool 'Claude Code' over a holiday break revealed a powerful adoption catalyst. Actually seeing an agent autonomously perform a complex task creates an 'aha moment' that makes AI's potential tangible, suggesting interactive demos are crucial for convincing decision-makers and accelerating enterprise buy-in.

To drive genuine AI transformation, leaders cannot just delegate. Zapier's executive team holds "AI show and tell" sessions where each member presents their own hands-on AI use cases. This demonstrates commitment, builds practical knowledge of AI's limits, and ensures leadership's vision is authentic.

To get teams to embrace AI, leaders should ditch generic mandates like "use more AI." Instead, focus on specific business transformations and highlight the customer value they create. Using company-wide forums for "show and tell" sessions where teams demonstrate unarguable successes makes adoption organic and outcome-driven, not a top-down chore.

When introducing AI to a skeptical executive, a detailed, multi-week rollout plan can be overwhelming and trigger resistance. A more effective approach is to showcase one specific AI capability within an existing tool to solve a tangible problem. This "dip your toe in the water" approach builds comfort and demonstrates immediate value.

Leaders, particularly CMOs, can't just mandate AI adoption. They must demonstrate its value by actively using AI tools themselves and sharing their processes and wins with their teams, which serves as a powerful motivator for company-wide adoption.

Iron Horse replaced typical business updates at the start of leadership meetings with a mandatory "show-and-tell" where each leader demonstrates what they've built with AI. This peer pressure fosters cross-functional inspiration, proving more effective than top-down mandates for driving company-wide adoption.